2-Chloro- and 2,6-dichloroanilines are useful as intermediates in the manufacture of a wide variety of chemical products including, for example, dyes, pharmaceuticals and agricultural chemicals. Unfortunately, 2-chloro and 2,6-dichloroanilines, optionally substituted in the 3-. 5-, and/or 6-position, are often not that easy to obtain. Because of the reactivity of the 4-position (para to the NH.sub.2 group), this position must be blocked and subsequently deprotected to prevent overchlorination. For example, 2,6-dichloro-3-methylaniline is presently manufactured from the acetanilide of m-toluidine in a multistep process (see O. G. Backeberg et al., J. Chem. Soc., 1943, 78-80; and H. C. Brimelow et al., J. Chem. Soc., 1951, 1208-1212) involving the following reaction sequence: ##STR1## The yields of the protection (i) and chlorination (iii) steps are relatively low and the use of chlorosulfonic acid and ammonia present difficulties with respect to safe handling and waste disposal.
This it is desirable to have a process for safely and more economically producing 2-chloro and 2,6-dichloroanilines in good yield from readily available starting materials.